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In a small saucepan or microwave-safe bowl, melt the butter.
Stir in brown sugar, cinnamon, salt, and vanilla until smooth and glossy.
Pour about ⅔ of the cinnamon goo into an 8×8-inch (2-quart) baking dish.
Place the dish in the oven and preheat to 450°F (232°C) until the goo is bubbling, about 4–5 minutes.
Set the remaining ⅓ goo aside.
In a large bowl, whisk together flour, salt, baking powder, and granulated sugar.
Add buttermilk and vanilla and gently stir until just combined.
The batter should be thick and slightly lumpy—do not overmix.
Carefully remove the hot baking dish from the oven.
Pour the biscuit batter evenly over the bubbling goo base (do not stir).
Drizzle the remaining cinnamon goo over the top of the batter.
Using a knife or skewer, gently swirl through the batter—staying mostly in the top and middle layers.
Sprinkle the cinnamon sugar evenly over the surface.
Lightly score the batter into 9 squares.
Bake 20–26 minutes, rotating once, until: the top is deep golden, the edges are bubbling with cinnamon goo, the center springs back when gently pressed.
If the top browns too quickly, tent loosely with foil.
Whisk together powdered sugar, milk, vanilla, and salt until smooth and pourable.
Let biscuits cool 5–10 minutes, then drizzle with glaze.
Serve warm for maximum gooeyness.